The High-Earner Hobby

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Fact # 1

Sherman presents a typical situation where a high-income taxpayer tries to use large personal expenditures to reduce that income by claiming the expenditures were for a business. In this case a high-income doctor created this homemade website (Op. at 4) called “Songswell.” At the bottom of the front page it says “Site created to showcase music to the world.” And not just any music, but Dr. Sherman’s music. Well, he has the freedom to do that. The site contains various short video clips of various water flows and audio clips of various water sounds. The showcase video is a man riding the “swell” of the ocean. Most of the video clips appear to feature Dr. Sherman playing the guitar and singing songs. The site appears to offer many of these clips for sale but when I clicked on the “buy” buttons I basically got a 404 error (page not found).

The year at issue is 2015. That year, Dr. Sherman worked as an emergency room physician, earning at least $143,000. He failed to file a tax return. In 2019 the IRS prepared a Substitute for Return based on third-party information returns and sent Dr. Sherman an NOD showing a tax deficiency of $60,000. That prompted him to file a return. It reported zero income from Songswell but some $105,00 in expenses, a big chunk of which was for specialized AV equipment, such as $51,000 for a “Alexa Mini Camera” and another $20,000 for “Alex[a] Mini Accessories.” You can watch this YouTube video to see what that system looks like. It’s pretty high-end.

Dr. Sherman petitioned the Tax Court (pro se) and claimed that the NOD was in error because (a) he should be allowed a deduction of $52,500 for expenses associated with his medical practice and (a) he should be allowed a deduction of $105,000 for the net loss he in incurred in Songswell, which he claimed was a business. The medical expense claims are not part of the lesson.

Lesson # 1- Keep Records-Have Income. 

How to build your personal credit

Judge Jones dutifully applies the WTF test and finds that each and every factor weighs against a finding that Songswell was a business. I recommend reading this opinion to get a good sense of how all the factors work. However, two factors were epic fails and give use our first lesson.

The first epic fail was that Dr. Sherman did not conduct the activity in a businesslike manner. That main problem was lack of adequate records. I mean, the man did not even keep basic receipts: “Dr. Sherman was unable to produce any documentation or receipts for most of the expenses listed in the “other” category... Further, although Dr. Sherman purchased some camera equipment and accessories in 2015, the amounts on the receipts do not match the expenses reported on Schedule C. Additionally, many of his equipment purchases occurred outside the 2015 taxable year.” Op. at 6.

But even if he had receipts, a taxpayer needs more than receipts to show they are conducting an activity in a businesslike manner. They need basic records of the business activity. Here, Dr. Sherman had none. He had no records to show a business plan or even to show “when Songswell activities began, nor precisely what activity occurred in taxable year 2015.”  Op. at 11.

The second epic fail was the total lack of income from Songswell and his substantial income from being a doctor. Writes Judge Jones: “His reported losses from Songswell—in addition to his medical practice expenses—would produce a substantial tax benefit, essentially zeroing out any tax obligation he owed.” Op. at 15.

Judge Jones concludes: “This is not a difficult case... Aside from Dr. Sherman’s self-serving testimony that the Songswell activity was conducted for profit, little else counsels in favor of finding a profit motive...” Op. at 10.



Bottom Line #1: Your vanity website is not a business if you have zero sales over multiple years.


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January 24, 2026
Inflation isn’t gone—it’s just quieter. Around 3% feels tame compared to the chaos of the past few years, but that doesn’t mean it’s harmless. For most business owners, small shifts in pricing, payroll, and supply costs have become the new normal—slow, steady pressure that eats into margins one percentage point at a time. But here’s the thing: inflation doesn’t just erode profit. It also creates permission. Permission to reprice. Permission to renegotiate. Permission to rethink how your business makes money. And as we head into year-end—when every business is reviewing budgets, forecasts, and compensation plans—now’s the perfect time to turn inflation from a problem into a strategic opportunity. The Inflation Mindset Shift: From Defense to Offense Most owners treat inflation like a storm to wait out. They hunker down, cut costs, and hope the economy stabilizes. But smart firms? They play offense. Inflation gives you the perfect narrative to reset pricing, refine operations, and re-anchor value with your clients or customers. Think about it: when everything costs more—from raw materials to insurance—people expect prices to adjust. That makes this moment the cleanest window you’ll get to implement changes that were overdue anyway. Step 1: Reprice With Confidence, Not Apology The biggest mistake small businesses make is treating price increases like confessions. “Sorry, but our costs went up.” Instead, reframe it as value alignment: “We’ve upgraded our processes, improved delivery, and invested in technology to serve you better.” Even if your costs are rising, your value probably has too. If your last price review was more than 18 months ago, you’re already behind. Inflation gives you cover to fix that. Step 2: Audit Margins and Cash Flow Before You Budget Before you finalize 2026 budgets, run a true margin audit. Which services or products are still profitable at today’s costs?
 Which are borderline or underwater?
 Which clients consistently underpay for the value delivered? Then connect that data to your cash flow forecast. A business that plans around real margins—versus assumptions—has control. If you haven’t reviewed vendor contracts lately, this is also your chance to lock in rates before potential tariff shifts or supply cost changes next year. Step 3: Forecast Smarter, Not Just Harder Forecasting isn’t about predicting inflation—it’s about being ready for it. Smart firms use 3-scenario forecasting: Best case: Inflation drops further, demand grows.
 Base case: 3% inflation continues, steady but modest growth.
 Stretch case: Tariffs increase, costs rise, and cash flow tightens. By modeling each, you build agility—not anxiety—into your business plan. Step 4: Align Compensation and Value Creation Inflation doesn’t just affect costs—it affects expectations. Employees feel it too. As you plan 2026 compensation, think about rewarding value creation instead of just cost-of-living bumps. For example: Introduce profit-sharing to align team success with performance.
 Offer flexible benefits like health stipends or hybrid schedules—high perceived value, lower cost.
 Communicate transparently about financial goals. Most teams handle reality better than silence. Step 5: Protect Profitability Before It’s a Problem When inflation was at 8%, you could blame it for shrinking profits. At 3%, it’s just math. That means you can’t afford to ignore the incremental hits—subscription creep, silent vendor increases, underpriced legacy clients. The businesses that thrive in 2026 will be the ones that use this “quiet inflation” window to: Trim inefficiencies before they compound.
 Rebuild reserves.
 Reinvest in tools that save time or improve margins (think automation, AI, or better client systems). The Big Idea: Inflation as a Reset Button You can’t control the economy—but you can control how your business responds to it. Inflation isn’t a crisis anymore. It’s your chance to reset the rules—on pricing, partnerships, and profitability. When you treat inflation as an opportunity, not a threat, you stop playing defense and start leading from strength. Ready to Plan Your 2026 Strategy? Now’s the time to review pricing, forecasting, and compensation plans before the new year begins. If you want to make 2026 your margin expansion year—not another squeeze—contact our firm. We’ll help you analyze your numbers, refine your strategy, and move into the new year with confidence and control.
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January 8, 2026
Growth Feels Great—Until It Doesn’t At first, running your business feels simple: money comes in, bills go out, and if there’s something left over, you’re doing fine. Then growth happens.
 More clients. Bigger projects. Higher payroll. Maybe even a second location. Suddenly, cash doesn’t flow the way it used to. You’re booking record sales, but your bank balance looks… thin. You’re working harder than ever, yet the pressure to make next week’s payments feels heavier. Welcome to the paradox of growth: the bigger your business gets, the tighter cash flow can feel. Why Growing Businesses Feel Cash-Poor It’s not bad management—it’s math. As revenue grows, so do: Accounts receivable: Clients take longer to pay larger invoices.
 Inventory or project costs: You spend cash weeks (or months) before you earn it back.
 Payroll: Growth usually means more people—and payroll hits like clockwork, even when customer payments don’t.
 Taxes: Higher profits mean higher estimated payments that pull cash out of your account quarterly.
 Growth stretches the timing gap between money going out and money coming in. Without a system to monitor and forecast it, you’re flying blind. The Shift: From Bookkeeping to Cash Flow Strategy Most small businesses start with simple bookkeeping: track what you earned, record what you spent, file the taxes. But once you grow, you need something more— cash flow management that looks ahead, not just backward. That’s where financial professionals make all the difference.

They can help you: Forecast inflows and outflows weeks or months in advance.
 Spot cash gaps early—and plan around them.
 Build reserves for seasonality or growth spurts.
 Model “what-if” scenarios (new hires, equipment purchases, expansions) before you commit. In other words, they help you turn growth from a guessing game into a system. Real-World Example: The Busy-but-Broke Dilemma One of our clients doubled revenue in a year—then almost ran out of cash. Why? Every big new contract required more up-front costs and staff before payments arrived. Once we mapped cash flow month by month, they saw the problem clearly. With a few tweaks—changing invoice terms, adjusting payroll timing, and setting up a short-term credit line—they moved from panic to predictability. The revenue didn’t change. The system did. Bottom Line Growth brings opportunity—but it also brings complexity. What used to fit on a spreadsheet now needs structure, foresight, and strategy. If your business is growing fast but cash feels tight, it’s time to move beyond basic bookkeeping.
Contact our firm today to build a cash flow plan that grows as smart as you do.
December 12, 2025
Are you ready to make the move? Are you looking for someone to help you grow your business? A CPA firm who cares about not only your business but you as a person? A firm which can bring insight into your business? One that looks out for your best interests while keeping you compliant with all the IRS, state and other financial regulations? If so, we are looking for you! Steven Brewer & Company, CPAs, is brick and mortar office with a strong virtual presence. We are looking for the right clients to join us. Currently we work with over 35 companies in 20 states. We know how to work virtually with our clients. We work to help you understand your business; help you plan for the future and use your business assets in planning for the best results in building your future. If you are looking for all of this, give us call (812-883-6938) or drop us an email (admin@stevenbrewercpa.com) to schedule a meeting to discuss your financial needs. In the meantime, check out our website, stevenbrewercpa.com, to find out more about us.